Ammonium formate → 8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200566Notes

Reaction equation

HRID 2200566 reaction equation
C([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][OH:21])[C:13](=[O:22])[N:12]([CH2:23][CH3:24])[C:11]=2[N:10]=[C:9]1[O:25][CH2:26][CH3:27])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:26]([O:25][C:9]1[NH:8][C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][OH:21])[C:13](=[O:22])[N:12]([CH2:23][CH3:24])[C:11]=2[N:10]=1)[CH3:27]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 904023587-benzyl-8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 904023668-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dioneYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

7-benzyl-8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (0.12 g, 0.323 mmol) was dissolved in ethanol (20 mL) and the mixture was degassed and refilled with nitrogen three times. Ammonium formate (0.5 g, 7.94 mmol) and 10% Pd/C (30 mg) were added. The mixture was again degassed and refilled with nitrogen three times; then it was warmed to 80° C. and stirred overnight. The mixture was cooled and filtered, and the filter cake was washed with methanol. The filtrate was concentrated to give 8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (70 mg, 77.1% yield) as white solid. LCMS retention time 0.413 min; LCMS MH+ 283.

Workup

  1. customthe mixture was degassed
  2. additionrefilled with nitrogen three times
  3. customThe mixture was again degassed
  4. additionrefilled with nitrogen three times
  5. temperatureThe mixture was cooled
  6. filtrationfiltered
  7. washthe filter cake was washed with methanol
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4b3602e0cc5144ee83b0a9db2c6b83ef
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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